Methanol → 4-Hydroxy-1-phenylcyclohexane-1-carbonitrile

HRID 596284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596284
CO.[C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)#[N:4].[BH4-].[Na+]>O1CCCC1>[C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)#[N:4]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 4311764Sodium borohydride

Produkt 1

HCID 124536734-Hydroxy-1-phenylcyclohexane-1-carbonitrileAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

to an ice and methanol cooled solution of 4 g. (0.0205 M) of 4-cyano-4-phenylcyclohexanone (a) (prepared as in J. Chem. Soc. 1959, 1446) in 150 ml. of tetrahydrofuran, a suspension of 1 g. of sodium borohydride in 50 ml. of tetrahydrofuran is added in 5 ml. portions in in the course of about 10 minutes. The mixture is stirred for about 30 minutes and allowed to stand in the cold for about 18 hours. The bulk of the solvent is removed under vacuum and the residue treated with water. The precipitate is extracted with ether and the organic fraction washed successively with 2.5 N hydrochloric acid solution, saturated aqueous sodium bicarbonate, water and brine and then evaporated to dryness. The residue is recrystallized with benzene to give 1.81 g. (43.8% yield) of 4-cyano-4-phenylcyclohexanol (b) melting at 103° to 111° C.

Aufarbeitung

  1. customin in the course of about 10 minutes
  2. customcold for about 18 hours
  3. customThe bulk of the solvent is removed under vacuum
  4. additionthe residue treated with water
  5. extractionThe precipitate is extracted with ether
  6. washthe organic fraction washed successively with 2.5 N hydrochloric acid solution, saturated aqueous sodium bicarbonate, water and brine
  7. customevaporated to dryness
  8. customThe residue is recrystallized with benzene
  9. customto give 1.81 g

Quellen und Nachweise

ORD-Eintrag
ord-29fd6a8fc20040439e156de2f5b662b5
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04010201

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